Incredible sailboat rentals in Maryland, United States.
1 - 18 of 21 listings
Charter this 42ft Hunter Passage Sailboat in Edgewater, Maryland and sail on the beautiful Chesapeake Bay
Rent or charter a sailboat for a memorable experience in Maryland.
Are you ready for a fun adventure out on the open water onboard a sailboat in Maryland? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Maryland is a wonderful sailboat rental destination.
Using GetMyBoat to book your next sailing experience.
Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.
Search for the perfect experience now and book your dream day out on the water.
Top destinations nearby
GetMyBoat customer reviews for Sailing in Maryland.
- CB
Cathy
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
We had a wonderful time sailing with Captain Alberto and his wife Grace! My husband and I and two of our friends went for an afternoon cruise as a birthday celebration. The boat was beautiful and they were friendly and gracious hosts. I was interested in learning more about sailing and Captain Alberto (an experienced sailing instructor) was a great teacher. Captain Alberto was also very responsive and helpful when we were making the arrangements for the trip. We hope to have an opportunity to do this again, and highly recommend a trip with Captain Alberto!
- KH
Karen
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Our group of 6 friends enjoyed a terrific sunset cruise on Captain Alberto's boat. Captain Alberto is clearly an experienced sailor. He and his lovely wife were both very welcoming and we really enjoyed their company. Overall it was a wonderful evening and we all highly recommend it!
- SL
Sarah
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
I booked this trip as a surprise birthday present for my fiancé! I invited a few of his friends and they all had a great time hanging out and learning a little about sailing. Captain Alberto and his wife were great and very knowledgeable. We would definitely recommend to anyone!
- NP
Nicole
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
We celebrated my friend's bachelorette party with a sailing adventure. Captain Alberto and his wife were absolutely wonderful. We had an amazing time on the boat and they were great hosts. The entire process was seamless and extremely enjoyable. They went above and beyond to make it such a great experience. I would highly recommend booking!!!
- MF
Molly
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Could not have asked for a better day on Captain Alberto's sailboat! My family and I had a wonderful time sailing across the bay, going for a quick swim and got a bonus tour of the Annapolis marina. Alberto and his wife were gracious hosts and let us have some time behind the wheel. It was such a treat sailing with such experienced individuals that will give you impromptu sailing tips and tricks. I highly recommend Captain Alberto for anyone looking to have a fun day on the bay and learn a thing or two about sailing!
- JM
Johannah
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
This was such a great experience!! I brought 4 friends on this boat for my birthday and it was perfect. We all brought snacks and drinks, our bathing suits and a reggae playlist to set us up for a relaxing and fun day. We got to participate in steering the ship, raising the mast, etc. and that was a really cool experience because I like to learn things. Also, Grace and Alberto were so genuine, adventurous, fun, kind and I could go on. I had the best time hearing their life stories and by the end of the trip our relationship felt way more like "old friends" than "customer". We also were able to pull over and swim which to me was the funnest part! I definitely recommend this experience and think it could be anything from "classy and romantic" to "casual and fun" depending on the event and what each group wants and time of day.